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WO1998017269A1 - Utilisation des sels de zinc d'acides linoleiques conjugues pour le traitement des maladies de la peau - Google Patents

Utilisation des sels de zinc d'acides linoleiques conjugues pour le traitement des maladies de la peau Download PDF

Info

Publication number
WO1998017269A1
WO1998017269A1 PCT/GB1997/002854 GB9702854W WO9817269A1 WO 1998017269 A1 WO1998017269 A1 WO 1998017269A1 GB 9702854 W GB9702854 W GB 9702854W WO 9817269 A1 WO9817269 A1 WO 9817269A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
conjugated linoleic
linoleic acid
zinc salt
skin disorders
Prior art date
Application number
PCT/GB1997/002854
Other languages
English (en)
Inventor
Derek Bryce-Smith
Original Assignee
Kappa Pharmaceuticals Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kappa Pharmaceuticals Limited filed Critical Kappa Pharmaceuticals Limited
Priority to JP51908498A priority Critical patent/JP4243353B2/ja
Priority to AT97909433T priority patent/ATE311871T1/de
Priority to US09/284,047 priority patent/US6300374B1/en
Priority to NZ334593A priority patent/NZ334593A/xx
Priority to AU47119/97A priority patent/AU718611B2/en
Priority to DE69734838T priority patent/DE69734838T2/de
Priority to EP97909433A priority patent/EP1014967B1/fr
Publication of WO1998017269A1 publication Critical patent/WO1998017269A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/28—Compounds containing heavy metals
    • A61K31/315—Zinc compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention concerns compositions and their use in the treatment of skin disorders particularly, but not limited, to eczema, psoriasis and dermatitis, and also compositions and their use in treatment of cancer, particularly skin cancer.
  • Conjugated linoleic acid and linoleic acid are well-known for their therapeutic, particularly chemotherapeutic, properties (see, for example, Belury, M.A., 1995 Nutrition Reviews, 53 (4) : 83-39 and references therein; Pariza, M.W., Chemistry & Industry, 16 June 1997, 464-466; EP 0 087 863; EP 0 044 341; EP 0 078 434; EP 0 003 407; EP 0 057 175; EP 0 071 357; EP 0 085 579; EP 0 139 480), and have comprised non-essential components of compositions for treating skin disorders (EP 0 727 991).
  • WO 95/13806 discloses the use of a composition comprising zinc salts of 68% (unconjugated) linoleic acid and 10% conjugated isomers of linoleic acid for use in treating skin disorders.
  • compositions for use in treating skin disorders comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • the composition may be used in a method of treating skin disorders.
  • compositions comprising substantially the zinc salt of at least one conjugated linoleic acid in the manufacture of a medicament for treating skin disorders.
  • a method of manufacture of a medicament for treating skin disorders comprising the use of a composition comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • Also provided is a method of treatment of a skin disorder comprising the use of a composition comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • compositions and medicaments of the present invention will be readily apparent to one skilled in the art and are exemplified in the Examples below.
  • the composition may comprise at least 50%, for example at least 60%. 70%, 80% or 90%, the zinc salt of at least one conjugated linoleic acid.
  • it may substantially comprise the zinc salt of a conjugated linoleic acid or it may comprise a substantially greater proportion of the zinc salt or salts of at least one conjugated linoleic acid than of zinc linoleate
  • the present inventor has found that the zinc salts of conjugated linoleic acids have a surprisingly great efficacy, compared to that of conjugated linoleic acids alone (which may act as irritants) and of zinc linoleate, when used in the treatment and/or prophylaxis of skin disorders such as eczema, psoriasis, cold sores (herpes) and dermatitis.
  • the conjugated linoleic acids are a large family of molecules. Dienoic conjugated linoleic acids may be used as the basis of the zinc salts of the present invention. For example, 9,11-octadecadienoic acid or 10,12-octadecadienoic acid may be used. These unsaturated molecules contain double bonds and so there are a number of geometric isomes of the molecules, for example cis9,trans ⁇ 1-octadecadienoic acid and trans9,cis ⁇ 1-octadecadienioc acid.
  • compositions of the present invention may be used in conjunction with a pharmaceutically acceptable carrier, diluent or excipient.
  • a pharmaceutically acceptable carrier diluent or excipient.
  • Such carriers, diluents and excipients are well known - see for example Remington's Pharmaceutical Sciences and US Pharmacopeia (1984) Mack Publishing Company, Easton, PA.
  • composition may also comprise at least one antioxidant, for example tocopherol (Vitamin E).
  • antioxidant for example tocopherol (Vitamin E).
  • the composition may also comprise for example zinc linoleate and/or the zinc salt of at least one other fatty acid.
  • Conjugated lioleic acids are usually prepared by the isomerisation of linoleic acid, and are therefore liable to contain various residues of linoleic acid.
  • zinc linoleate may be among the zinc salts formed when the isomerised linoleic acid is converted into zinc salts.
  • the zinc salts of conjugated linoleic acids appear to be more effective than zinc salts of other fatty acids, and (see examples B and C below) do not owe their activity to the presence of zinc alone.
  • Medicaments and compositions according to the present invention may be administered in doses (i.e. concentrations and quantities) sufficient to effect the desired prophylactic or therapeutic result. Such doses may be readily determined using simple dose-response experiments.
  • the doses may be such that they are substantially non-irritant to the patient.
  • a composition for use in treating cancer comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • the composition may be used in a method of treating cancer.
  • composition comprising substantially the zinc salt of at least one conjugated linoleic acid in the manufacture of a medicament for treating cancer.
  • Also provided is a method of manufacture of a medicament for treating cancer comprising the use of a composition comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • Also provided is a method of treatment of a cancer comprising the use of a composition comprising substantially the zinc salt of at least one conjugated linoleic acid.
  • compositions and medicaments of the present invention will be readily apparent to one skilled in the art, particularly with reference to the Examples below.
  • the composition may comprise at least 50%, for example at least 60%. 70%, 80% or 90%, the zinc salt of at least one conjugated linoleic acid.
  • it may substantially comprise the zinc salt of a conjugated linoleic acid or it may comprise a substantially greater proportion of the zinc salt or salts of at least one conjugated linoleic acid than of zinc linoleate.
  • a zinc salt may for example be of 9,11-octadecadienoic acid or 10,12- octadecadienoic acid.
  • the zinc salts of the compositions of the present invention for the treatment and/or prophylaxis of skin disorders also appear to be useful in the treatment and/or prophylaxis of cancer, particularly epidermal cancers such as skin cancer.
  • the medicament may additionally comprising a pharmaceutically acceptable carrier, diluent or excipient.
  • ZCL zinc conjugated linoleates
  • the physical characteristics of the product were varied by increasing or decreasing the proportion of water during the preparation. One half of the above proportion of water gave an ointment, whereas increasing the proportion of water by 50% gave a cream.
  • Example B A male patient suffering from eczema, mainly on the arms, was treated by daily topical application of the ZCL semi-cream of Example A. The condition was completely cured within 4 days.
  • Example A The product prepared as in Example A was used to treat a female patient suffering from facial psoriasis. This condition was greatly improved within 1 day and essentially cured within 2 days.
  • a male patient aged 70 years suffering from pruritus of the legs and scalp was treated by topical application of a semi-cream prepared as in Example A. Itching ceased within 10- 15 minutes.
  • Example H A female patient of 55 years age suffered severe discomfort caused by pressure sores on the trunk. A single application of the semi-cream of Example A rapidly alleviated all soreness and discomfort.
  • Example H A female patient of 55 years age suffered severe discomfort caused by pressure sores on the trunk. A single application of the semi-cream of Example A rapidly alleviated all soreness and discomfort.
  • Example A A male patient of 55 years age suffered from an erupted (i.e. broken skin) cold sore (Herpes). Treatment with the semi-cream of Example A rapidly removed the soreness and discomfort, and the condition was essentially cured within 2 days.
  • a male patient suffering from skin cancer applied the semi-cream of Example A on a daily basis to an area of skin cancer. Over a period of four months, the appearance of the affected area improved (although the cancer did not totally disappear) and itching of the affected area stopped. Discontinuation of treatment resulted in the recurrence of itching at the affected area.
  • a female patient had a patch of discoloured skin on one ankle which was medically diagnosed as skin cancer.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

Cette invention a pour objet des compositions et leur utilisation dans le traitement des maladies de la peau, entre autres l'eczéma, le psoriasis et les dermatoses, ainsi que des compositions et leur utilisation pour le traitement du cancer, en particulier le cancer de la peau.
PCT/GB1997/002854 1996-10-17 1997-10-16 Utilisation des sels de zinc d'acides linoleiques conjugues pour le traitement des maladies de la peau WO1998017269A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP51908498A JP4243353B2 (ja) 1996-10-17 1997-10-16 皮膚疾患の治療に用いる共役リノール酸の亜鉛塩
AT97909433T ATE311871T1 (de) 1996-10-17 1997-10-16 Verwendung von zinksalzen der konjugierten linoleinsäuren zur behandlung von hautkrankheiten
US09/284,047 US6300374B1 (en) 1996-10-17 1997-10-16 Use of zinc salts of conjugated linoleic acid to treat skin disorders
NZ334593A NZ334593A (en) 1996-10-17 1997-10-16 Use of zinc salts of conjugated linoleic acids to treat skin disorders particularly eczema, psoriasis and dermatitis and their use in the treatment of skin cancer
AU47119/97A AU718611B2 (en) 1996-10-17 1997-10-16 Use of zinc salts of conjugated linoleic acids to treat skin disorders
DE69734838T DE69734838T2 (de) 1996-10-17 1997-10-16 Verwendung von zinksalzen der konjugierten linoleinsäuren zur behandlung von hautkrankheiten
EP97909433A EP1014967B1 (fr) 1996-10-17 1997-10-16 Utilisation des sels de zinc d'acides linoleiques conjugues pour le traitement des maladies de la peau

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9621630.4A GB9621630D0 (en) 1996-10-17 1996-10-17 Treatment of skin disorders
GB9621630.4 1996-10-17

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/568,305 Continuation US6288115B1 (en) 1996-10-17 2000-05-09 Use of zinc salts of conjugated linoleic acids to treat skin disorders

Publications (1)

Publication Number Publication Date
WO1998017269A1 true WO1998017269A1 (fr) 1998-04-30

Family

ID=10801560

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1997/002854 WO1998017269A1 (fr) 1996-10-17 1997-10-16 Utilisation des sels de zinc d'acides linoleiques conjugues pour le traitement des maladies de la peau

Country Status (10)

Country Link
US (2) US6300374B1 (fr)
EP (1) EP1014967B1 (fr)
JP (1) JP4243353B2 (fr)
AT (1) ATE311871T1 (fr)
AU (1) AU718611B2 (fr)
DE (1) DE69734838T2 (fr)
ES (1) ES2253772T3 (fr)
GB (1) GB9621630D0 (fr)
NZ (1) NZ334593A (fr)
WO (1) WO1998017269A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999026588A3 (fr) * 1997-11-21 1999-07-22 Natural Nutrition Ltd As Systeme d'apport d'acide linoleique conjugue dans des preparations cosmetiques
WO2000037040A1 (fr) * 1998-12-22 2000-06-29 Unilever Plc Compositions pour les soins de la peau contenant un acide linoleique cis 9 trans 11
WO2000037039A1 (fr) * 1998-12-22 2000-06-29 Unilever Plc Composition eclaircissante pour la peau
FR2802099A1 (fr) * 1999-12-08 2001-06-15 Fabre Pierre Cosmetique Thiosalicylate de zinc, compositions dermatologiques le contenant, en particulier sous la forme d'un dispositif auto-adhesif ainsi que le procede de preparation de ce dernier
WO2001085161A1 (fr) * 2000-05-05 2001-11-15 Fresenius Kabi Deutschland Gmbh Preparation combinant des acides gras φ-3 et des acides linoleniques conjugues pour le traitement de maladies caracterisees par des tableaux cliniques a composante immunologique marquee
WO2001003688A3 (fr) * 1999-07-09 2002-06-20 Pharmacia Corp Traitement de troubles induits par une cycloxygenase-2 au moyen de composes a base d'acides gras conjugues
JP2003505490A (ja) * 1999-07-30 2003-02-12 ユニリーバー・ナームローゼ・ベンノートシヤープ 皮膚保護組成物
JP2003505492A (ja) * 1999-07-30 2003-02-12 ユニリーバー・ナームローゼ・ベンノートシヤープ スキンケア組成物
EP1162934A4 (fr) * 1999-02-22 2005-01-26 Eric F Bernstein Compositions et procedes de prevention du photovieillissement
US6953583B1 (en) 1999-09-09 2005-10-11 Pentapharm Ag Use of conjugated linoleic acid (CLA) for the topical treatment of cellulite
WO2005107736A1 (fr) * 2004-05-11 2005-11-17 Fonterra Corporate Research And Development Limited Matiere grasse de lait enrichie au cla et utilisation de celle-ci
WO2007055599A1 (fr) * 2005-11-10 2007-05-18 Fonterra Corporate Research And Development Limited Compositions d'acide cis-9,trans-11-linoleique conjugue et d'acide vaccenique et utilisations de celles-ci
US8975295B2 (en) 2002-10-25 2015-03-10 Precision Dermatology, Inc. Modulation of zinc levels to improve tissue properties

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030143165A1 (en) * 2002-01-25 2003-07-31 Allan Evans NSAID-containing topical formulations that demonstrate chemopreventive activity
TW200407172A (en) * 2002-10-17 2004-05-16 Unilever Nv Scalp treatment
US7767713B2 (en) * 2004-08-05 2010-08-03 Palo Alto Investors Linoleic acid active agents for enhancing probability of becoming pregnant

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ92493A3 (en) * 1993-05-17 1994-12-15 Stol Miroslav Healing composition for topic external application
WO1995013806A1 (fr) * 1993-11-18 1995-05-26 Kappa Pharmaceuticals Limited Compositions contenant du linoleate de zinc et servant a traiter des maladies de peau

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
US6025334A (en) * 1994-04-28 2000-02-15 Les Laboratoires Aeterna Inc. Extracts of shark cartilage having anti-collagenolytic, anti-inflammatory, anti-angiogenic and anti-tumoral activities; process of making, methods of using and compositions thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ92493A3 (en) * 1993-05-17 1994-12-15 Stol Miroslav Healing composition for topic external application
WO1995013806A1 (fr) * 1993-11-18 1995-05-26 Kappa Pharmaceuticals Limited Compositions contenant du linoleate de zinc et servant a traiter des maladies de peau

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9507, Derwent World Patents Index; AN 95-044024, XP002053010 *
M.A. BELURY ET AL.: "Dietary conjugated linoleic acid modulation of phorbol ester skin tumor promotion.", NUTR. CANCER, vol. 26, no. 2, 1996, pages 149 - 157, XP002053009 *
P.W.PARODI: "Conjugated linoleic acid: an anticarcinogenic fatty acid present in milk fat.", AUSTRALIAN J. DIET. TECHNOL., vol. 49, no. 2, 1994, pages 93 - 97, XP002053008 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999026588A3 (fr) * 1997-11-21 1999-07-22 Natural Nutrition Ltd As Systeme d'apport d'acide linoleique conjugue dans des preparations cosmetiques
WO2000037040A1 (fr) * 1998-12-22 2000-06-29 Unilever Plc Compositions pour les soins de la peau contenant un acide linoleique cis 9 trans 11
WO2000037039A1 (fr) * 1998-12-22 2000-06-29 Unilever Plc Composition eclaircissante pour la peau
CZ302773B6 (cs) * 1998-12-22 2011-11-02 Unilever N. V. Topický prostredek obsahující cis 9, trans 11 kyselinu linolovou pro lécení kuže
AU746697B2 (en) * 1998-12-22 2002-05-02 Unilever Plc Skin lightening composition
US6403064B1 (en) 1998-12-22 2002-06-11 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Skin lightening composition
EP1162934A4 (fr) * 1999-02-22 2005-01-26 Eric F Bernstein Compositions et procedes de prevention du photovieillissement
WO2001003688A3 (fr) * 1999-07-09 2002-06-20 Pharmacia Corp Traitement de troubles induits par une cycloxygenase-2 au moyen de composes a base d'acides gras conjugues
JP2003505492A (ja) * 1999-07-30 2003-02-12 ユニリーバー・ナームローゼ・ベンノートシヤープ スキンケア組成物
JP2003505490A (ja) * 1999-07-30 2003-02-12 ユニリーバー・ナームローゼ・ベンノートシヤープ 皮膚保護組成物
US6953583B1 (en) 1999-09-09 2005-10-11 Pentapharm Ag Use of conjugated linoleic acid (CLA) for the topical treatment of cellulite
WO2001041702A3 (fr) * 1999-12-08 2001-12-06 Fabre Pierre Dermo Cosmetique Thiosalicylate de zinc, compositions dermatologiques le contenant, en particulier sous la forme d'un dispositif autoadhesif ainsi que le procede de preparation de ce dernier
FR2802099A1 (fr) * 1999-12-08 2001-06-15 Fabre Pierre Cosmetique Thiosalicylate de zinc, compositions dermatologiques le contenant, en particulier sous la forme d'un dispositif auto-adhesif ainsi que le procede de preparation de ce dernier
WO2001085161A1 (fr) * 2000-05-05 2001-11-15 Fresenius Kabi Deutschland Gmbh Preparation combinant des acides gras φ-3 et des acides linoleniques conjugues pour le traitement de maladies caracterisees par des tableaux cliniques a composante immunologique marquee
US8975295B2 (en) 2002-10-25 2015-03-10 Precision Dermatology, Inc. Modulation of zinc levels to improve tissue properties
WO2005107736A1 (fr) * 2004-05-11 2005-11-17 Fonterra Corporate Research And Development Limited Matiere grasse de lait enrichie au cla et utilisation de celle-ci
WO2007055599A1 (fr) * 2005-11-10 2007-05-18 Fonterra Corporate Research And Development Limited Compositions d'acide cis-9,trans-11-linoleique conjugue et d'acide vaccenique et utilisations de celles-ci

Also Published As

Publication number Publication date
EP1014967B1 (fr) 2005-12-07
NZ334593A (en) 2000-01-28
DE69734838T2 (de) 2006-08-17
JP4243353B2 (ja) 2009-03-25
US6300374B1 (en) 2001-10-09
US6288115B1 (en) 2001-09-11
AU4711997A (en) 1998-05-15
JP2001502346A (ja) 2001-02-20
GB9621630D0 (en) 1996-12-11
DE69734838D1 (de) 2006-01-12
EP1014967A1 (fr) 2000-07-05
AU718611B2 (en) 2000-04-20
ES2253772T3 (es) 2006-06-01
ATE311871T1 (de) 2005-12-15

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